Heat the bacon over medium heat in a large pot or Dutch oven. Once the bacon turns crispy, remove about ΒΌ of the bacon and set it aside.
Add onions and fry in the bacon drippings. Stir in the allspice.
Add the diced butternut squash and apples. Stir well to combine with the bacon and onions. Cover with a lid and simmer for 1-2 minutes.
Pour the chicken broth and the heavy cream into the pot. Place the lid back on and bring the soup to a rapid boil. Reduce the heat and simmer for 10-15 or until the butternut squash and apples are tender.
Use an immersion blender and puree the soup until smooth. Season to taste with salt and pepper. Serve immediately and garnish with reserved bacon bits.